N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzamide → 3-amino-N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzamide

HRID 883681Notes

Reaction equation

HRID 883681 reaction equation
[CH2:1]([N:5]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:6](=[O:30])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:26])[CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=2)=[C:9]([N+:27]([O-])=O)[CH:8]=1)[CH:2]([CH3:4])[CH3:3]>[Pd].C(OCC)(=O)C.C(O)C>[NH2:27][C:9]1[CH:8]=[C:7]([CH:12]=[CH:11][C:10]=1[NH:13][CH2:14][CH2:15][CH2:16][N:17]([CH3:26])[CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1)[C:6]([N:5]([CH2:1][CH:2]([CH3:3])[CH3:4])[CH2:31][CH:32]([CH3:34])[CH3:33])=[O:30]

Participants

4

Reactant 1

HCID 69029055N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzamide

Product 1

HCID 690267883-amino-N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

N,N-diisobutyl-4-({3-[methyl(2-pyridin-2-ylethyl)amino]propyl}amino)-3-nitrobenzamide (2.9 g) in solution in an ethyl acetate/ethanol mixture (100 ml), and 10% palladium on carbon (290 mg) are added together in an autoclave. After stirring for 7 hours under a hydrogen atmosphere (3 bars), the catalyst is eliminated by filtration on Celite and the filtrate is concentrated under reduced pressure at 40° C. in order to produce the expected compound in the form of an oil (2.5 g, 92% yield).

Workup

  1. filtrationthe catalyst is eliminated by filtration on Celite
  2. concentrationthe filtrate is concentrated under reduced pressure at 40° C. in order

Sources & evidence

ORD record
ord-61d551df8fea42a7ae6552f2290df65e
Source dataset
uspto-grants-2012_08
Patent number
US08236965B2

Reaction notes

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